Diamond Head Oahu

Oahu Vacation Packages

 
Oahu, "The Gathering Place", is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cusine. On the northen side of the island, the surfer's paradise of North Shore, home of the Banzi pipeline and scenic rainforests offers a laid back island style visitors are sure to enjoy. To the West, Pearl Harbor is steeped in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture give Oahu a flavor all its own. Enjoy the best Oahu deals on Hawaii vacation packages today!
Get Ready for HAWAII
Welcoming Visitors Starting August 1, 2020
  • Travelers are required to present proof of a negative COVID-19 test within 72 hours of travel
  • Travelers without proof of a negative COVID-19 test will be required to quarantine for 14 days

Hawaii - FREE 5-day, two-category Hertz car rental upgrade
from midsize to luxury, convertible, Jeep or SUV

Book by 8/30/20 for travel through 4/30/21
Hertz logo
  • Moana Surfrider, A Westin Resort & Spa
    Moana Surfrider, A Westin Resort & Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This legendary resort, "The First Lady of Waikiki," combines turn-of the-century Victorian elegance with modern Westin amenities and luxuries.

    Book Now
  • Outrigger Waikiki Beach Resort
    Outrigger Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    “Where the Beach Comes Alive” Our extended ohana (family) will discover local beach and surf culture at this hotel on Waikiki Beach.

    Book Now
  • Outrigger Reef Waikiki Beach Resort
    Outrigger Reef Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    "Sharing the Arts & Culture of Hawaii" This distinctive, refined hotel presents a new vision of hospitality, combining timeless traditions with modern elegance.

    Book Now
  • Sheraton Princess Kaiulani
    Sheraton Princess Kaiulani
    Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Experience comfort and relaxation in the heart of Waikiki at this hotel while enjoying an exceptional vacation value.

    Book Now
  • Waikiki Beachcomber by Outrigger
    Waikiki Beachcomber by Outrigger
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    "An Oasis in the Heart of Waikiki" This brand new lifestyle resort which just completed a $35 million modernization offers contemporary comfort, camaraderie and fun.

    Book Now
  • Ilikai Hotel & Luxury Suites
    Ilikai Hotel & Luxury Suites
    Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    Ilikai Hotel & Luxury Suites is a historic high-rise set above the spectacular Waikiki shoreline.

    Book Now
Hawaii Two-Category Hertz Car Rental Upgrade Offer: Valid on new bookings made 07/06/2020 – 08/30/2020 for travel 07/06/2020 – 04/30/2021. Roundtrip airfare and minimum 5 nights’ hotel accommodation at participating hotel required. Age restrictions apply for car rental. Upgrade is from Midsize to Convertible, Jeep, Luxury or SUV for five days.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]